Ammonium Chloride → HCID 67528783, compound

HRID 2382873Notes

Reaction equation

HRID 2382873 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]([CH3:26])=[CH:22]B(O)O.[F-].[Cs+].[NH4+].[Cl-:30]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C1COCC1>[ClH:1].[ClH:30].[CH3:22][C:21]([CH3:26])=[CH:20][C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 25953Cesium fluorideHCID 27632992,2-Dimethylethenylboronic acidHCID 25212516N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide

Product 1

HCID 67528783HCID 67528783, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

N-(5-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide ((B4), 141.00 mg; 0.52 mmol; 1.00 eq.), 2,2-dimethylethenylboronic acid (Synthonix, 102.96 mg; 1.03 mmol; 2.00 eq.), cesium fluoride (156.53 mg; 1.03 mmol; 2.00 eq.) and bis(triphenylphosphine)palladium(II) chloride (36.16 mg; 0.05 mmol; 0.10 eq.) were flushed with nitrogen in a sealed vial. THF (degassed with nitrogen, 1.50 mL) and water (1 mL) were then added and the mixture was heated at 120° C., O/N in an oil bath. A solution of saturated NH4Cl was added and the reaction mixture was extracted with EtOAc (twice). Combined Organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give 186 mg of a yellow foam. Hydrochloride salt was then obtained by addition of Et2O/HCl (1 M solution) to a solution of this crude in DCM. The precipitate obtained was filtered and dried under vacuum at 40° C. to give the title compound as a beige solid (181 mg, 96%). HPLC, Rt: 2.05 min. (purity 92.3%). LC/MS, M+(ESI): 293.9, M−(ESI): 291.9.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc (twice)
  2. washCombined Organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a08601cf2da54552822d6bfa7024c571
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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